Solid Phase Synthesis in Water-Development of Green Chemistry

水固相合成——绿色化学的发展

• 批准号: 14572024
• 负责人: KAWASAKI Koichi
• 金额: $ 2.05万
• 依托单位: Kobe Gakuin University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2002
• 资助国家: 日本
• 起止时间: 2002 至 2004
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-14572024/
• 关键词: solid phase synthesis; peptide synthesis; green chemistry; Leu-enkephalin; water-soluble protecting group; water; 水中合成; 2-(4-sulfophenyl)ethoxycarbonyl group; 水中固相合成; エンケファリン; 水溶性保護アミノ酸; 水系固相法合成; 2-[phenyl(methyl)sulfonio]eyhoxycarbonyl基

Solid phase peptide synthesis (SPPS) is a well-established technique for the facile and rapid preparation of peptides, but it requires large amounts of organic solvents. Since the safe disposal of organic solvents is an important environmental issue, the ability to synthesize peptides in an aqueous medium would be preferable. In order to do so, water-soluble N-protected amino acids are necessary. We have successfully used the water-soluble N-protecting groups, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl (Pms), ethanesulfonylethoxycarbonyl (Esc) and 2-(4-sulfophenylsulfonyl)ethoxycarbonyl (Sps), for the SPPS of Leu-enkephalin amide in water.

固相多肽合成(SPPS)是一种简便、快速的多肽制备技术，但它需要大量的有机溶剂。由于有机溶剂的安全处理是一个重要的环境问题，因此能够在水介质中合成多肽将是更好的选择。为了做到这一点，水溶氮保护氨基酸是必需的。我们成功地利用了2-[苯基(甲基)磺基]乙氧基(PMS)、乙烷磺酰乙氧基(ESC)和2-(4-磺基苯磺酰基)乙氧基(SPS)等N-保护基团对亮氨酸脑啡酰胺在水中的SPPS进行了研究。

项目成果

A New Reagent, 2-[Phenyl(methyl)sulfonio]ethyl-4-nitro-phenylcarbonate Tetrafluoroborate (Pms-ONp), for Prepareing Water-Soluble N-Protected Amino Acids.

一种用于制备水溶性 N-保护氨基酸的新试剂 2-[苯基(甲基)磺酰基]乙基-4-硝基-苯基碳酸酯四氟硼酸盐 (Pms-ONp)。

• 发表时间: 2003
• 期刊: Peptide Science 2002 (Edited by Yamada, T.)(PROTEIN RESEARCH FOUNDATION, Minoh-shi, Japan)
• 作者: Hojo;K.;Maeda;M.;Kawasaki;K.
• 通讯作者: K.

Design of reagents for preparing water-soluble N-protected amino acids.

制备水溶性N-保护氨基酸的试剂设计。

• 发表时间: 2005
• 期刊: Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Libraries 2004 (Edited by Epton, R.)(Mayflower Wordwide Limited, London, England, UK)
• 作者: Hojo;K.;Maeda;M.;Kawasaki;K.
• 通讯作者: K.

A Water Soluble N-Protecting Group, 2-[Phenyl(methyl)-sulphonio]ethyloxycarbonyl Tetrafluoroborate and Its Application to Solid Phase Peptide Synthesis in Water.

水溶性N-保护基2-[苯基(甲基)-磺酰基]乙氧基羰基四氟硼酸盐及其在水中固相肽合成中的应用。

• 发表时间: 2003
• 期刊: Innovation and Perspectives in Solid Phase Synthesis & Combinatrial Libraries 2002 (Edited by Epton, R.)(Mayflower Wordwide Limited, Kingswinford, England)
• 作者: Hojo;K.;Maeda;M.;Kawasaki;K.
• 通讯作者: K.

Solid-phase synthesis in water. Part 3 : A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water

水中固相合成。

• 发表时间: 2004
• 期刊: Tetrahedron 60
• 作者: Keiko Hojo;Mitsuko Maeda;Koichi Kawasaki
• 通讯作者: Koichi Kawasaki

Keiko Hojo, Mitsuko Maeda, Timothy J.Smith, Eriko Kita, Fumie Yamaguchi, Sachiko Yamamoto, Koichi Kawasaki: "Peptide synthesis in water IV. Preparation of N-ethanesulfonylethoxy-Carbonyl (Esc) amino acids and their application to solid phase peptide synth

Keiko Hojo、Mitsuko Maeda、Timothy J.Smith、Eriko Kita、Fumie Yamaguchi、Sachiko Yamamoto、Koichi Kawasaki：“水中肽合成 IV. N-乙磺酰乙氧基羰基 (Esc) 氨基酸的制备及其在固相肽合成中的应用